The K‑Region in Pyrenes as a Key Position to Activate Aggregation-Induced Emission: Effects of Introducing Highly Twisted N,N‑Dimethylamines

A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly twisted N,N-dialkylamines of anthracene and naphthalene induce drastic AIE when these donors are introduced at appropriate positions to stabilize...

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Published inJournal of organic chemistry Vol. 82; no. 13; pp. 6865 - 6873
Main Authors Sasaki, Shunsuke, Suzuki, Satoshi, Igawa, Kazunobu, Morokuma, Keiji, Konishi, Gen-ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.07.2017
Amer Chemical Soc
Subjects
acetonitrile
anthracenes
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
energy
fluorescence
materials science
naphthalene
organic chemistry
Physical Sciences
Science & Technology
SUBSTITUTION
METAL-ORGANIC FRAMEWORKS
POLYCYCLIC AROMATIC-HYDROCARBONS
CONICAL INTERSECTION
FLUORESCENCE QUANTUM YIELDS
SOLID-STATE FLUORESCENCE
C-H BORYLATION
PHOTOPHYSICAL PROPERTIES
CHARGE-TRANSFER
DERIVATIVES
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Abstract A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly twisted N,N-dialkylamines of anthracene and naphthalene induce drastic AIE when these donors are introduced at appropriate positions to stabilize the S1/S0 minimum energy conical intersection (MECI). In the present study, this design strategy was applied to pyrene: the introduction of N,N-dimethylamine substituents at the 4,5-positions of pyrene, the so-called K-region, are likely to stabilize MECIs. To examine this hypothesis, four novel pyrene derivatives, which contain highly twisted N,N-dimethylamino groups at the 4- (4-Py), 4,5- (4,5-Py), 1- (1-Py), or 1,6-positions (1,6-Py) were tested. The nonradiative transitions of 4,5-Py are highly efficient (k nr = 57.1 × 107 s–1), so that its fluorescence quantum yield in acetonitrile decreases to Φfl = 0.04. The solid-state fluorescence of 4,5-Py is efficient (Φfl = 0.49). In contrast, 1,6-Py features strong fluorescence (Φfl = 0.48) with a slow nonradiative transition (k nr = 11.0 × 107 s–1) that is subject to severe quenching (Φfl = 0.03) in the solid state. These results underline that the chemistry of the pyrene K-region is intriguing, both from a photophysical perspective and with respect to materials science.
AbstractList A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly twisted N,N-dialkylamines of anthracene and naphthalene induce drastic AIE when these donors are introduced at appropriate positions to stabilize the S /S minimum energy conical intersection (MECI). In the present study, this design strategy was applied to pyrene: the introduction of N,N-dimethylamine substituents at the 4,5-positions of pyrene, the so-called K-region, are likely to stabilize MECIs. To examine this hypothesis, four novel pyrene derivatives, which contain highly twisted N,N-dimethylamino groups at the 4- (4-Py), 4,5- (4,5-Py), 1- (1-Py), or 1,6-positions (1,6-Py) were tested. The nonradiative transitions of 4,5-Py are highly efficient (k = 57.1 × 10 s ), so that its fluorescence quantum yield in acetonitrile decreases to Φ = 0.04. The solid-state fluorescence of 4,5-Py is efficient (Φ = 0.49). In contrast, 1,6-Py features strong fluorescence (Φ = 0.48) with a slow nonradiative transition (k = 11.0 × 10 s ) that is subject to severe quenching (Φ = 0.03) in the solid state. These results underline that the chemistry of the pyrene K-region is intriguing, both from a photophysical perspective and with respect to materials science.
A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly twisted N,N-dialkylamines of anthracene and naphthalene induce drastic AIE when these donors are introduced at appropriate positions to stabilize the S1/S0 minimum energy conical intersection (MECI). In the present study, this design strategy was applied to pyrene: the introduction of N,N-dimethylamine substituents at the 4,5-positions of pyrene, the so-called K-region, are likely to stabilize MECIs. To examine this hypothesis, four novel pyrene derivatives, which contain highly twisted N,N-dimethylamino groups at the 4- (4-Py), 4,5- (4,5-Py), 1- (1-Py), or 1,6-positions (1,6-Py) were tested. The nonradiative transitions of 4,5-Py are highly efficient (knr = 57.1 × 107 s-1), so that its fluorescence quantum yield in acetonitrile decreases to Φfl = 0.04. The solid-state fluorescence of 4,5-Py is efficient (Φfl = 0.49). In contrast, 1,6-Py features strong fluorescence (Φfl = 0.48) with a slow nonradiative transition (knr = 11.0 × 107 s-1) that is subject to severe quenching (Φfl = 0.03) in the solid state. These results underline that the chemistry of the pyrene K-region is intriguing, both from a photophysical perspective and with respect to materials science.A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly twisted N,N-dialkylamines of anthracene and naphthalene induce drastic AIE when these donors are introduced at appropriate positions to stabilize the S1/S0 minimum energy conical intersection (MECI). In the present study, this design strategy was applied to pyrene: the introduction of N,N-dimethylamine substituents at the 4,5-positions of pyrene, the so-called K-region, are likely to stabilize MECIs. To examine this hypothesis, four novel pyrene derivatives, which contain highly twisted N,N-dimethylamino groups at the 4- (4-Py), 4,5- (4,5-Py), 1- (1-Py), or 1,6-positions (1,6-Py) were tested. The nonradiative transitions of 4,5-Py are highly efficient (knr = 57.1 × 107 s-1), so that its fluorescence quantum yield in acetonitrile decreases to Φfl = 0.04. The solid-state fluorescence of 4,5-Py is efficient (Φfl = 0.49). In contrast, 1,6-Py features strong fluorescence (Φfl = 0.48) with a slow nonradiative transition (knr = 11.0 × 107 s-1) that is subject to severe quenching (Φfl = 0.03) in the solid state. These results underline that the chemistry of the pyrene K-region is intriguing, both from a photophysical perspective and with respect to materials science.
A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly twisted N,N-dialkylamines of anthracene and naphthalene induce drastic AIE when these donors are introduced at appropriate positions to stabilize the S1/S0 minimum energy conical intersection (MECI). In the present study, this design strategy was applied to pyrene: the introduction of N,N-dimethylamine substituents at the 4,5-positions of pyrene, the so-called K-region, are likely to stabilize MECIs. To examine this hypothesis, four novel pyrene derivatives, which contain highly twisted N,N-dimethylamino groups at the 4- (4-Py), 4,5- (4,5-Py), 1- (1-Py), or 1,6-positions (1,6-Py) were tested. The nonradiative transitions of 4,5-Py are highly efficient (k nr = 57.1 × 107 s–1), so that its fluorescence quantum yield in acetonitrile decreases to Φfl = 0.04. The solid-state fluorescence of 4,5-Py is efficient (Φfl = 0.49). In contrast, 1,6-Py features strong fluorescence (Φfl = 0.48) with a slow nonradiative transition (k nr = 11.0 × 107 s–1) that is subject to severe quenching (Φfl = 0.03) in the solid state. These results underline that the chemistry of the pyrene K-region is intriguing, both from a photophysical perspective and with respect to materials science.
A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly twisted N,N-dialkylamines of anthracene and naphthalene induce drastic AIE when these donors are introduced at appropriate positions to stabilize the S-1/S-0 minimum energy conical intersection (MECI). In the present study, this design strategy was applied to pyrene: the introduction of N,N-dimethylamine substituents at the 4,5-positions of pyrene, the so-called K-region, are likely to stabilize MECIs. To examine this hypothesis, four novel pyrene derivatives, which contain highly twisted N,N-dimethylamino groups at the 4- (4-Py), 4,5- (4,5-Py), 1- (1-Py), or 1,6-positions (1,6-Py) were tested. The nonradiative transitions of 4,5-Py are highly efficient (k(nr) = 57.1 x 10(7) s(-1)), so that its fluorescence quantum yield in acetonitrile decreases to Phi(fl) = 0.04. The solid-state fluorescence of 4,5-Py is efficient (Phi(fl) = 0.49). In contrast, 1,6-Py features strong fluorescence (Phi(fl) = 0.48) with a slow nonradiative transition (k(nr) = 11.0 x 10(7) s(-1)) that is subject to severe quenching (Phi(fl) = 0.03) in the solid state. These results underline that the chemistry of the pyrene K-region is intriguing, both from a photophysical perspective and with respect to materials science.
A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly twisted N,N-dialkylamines of anthracene and naphthalene induce drastic AIE when these donors are introduced at appropriate positions to stabilize the S₁/S₀ minimum energy conical intersection (MECI). In the present study, this design strategy was applied to pyrene: the introduction of N,N-dimethylamine substituents at the 4,5-positions of pyrene, the so-called K-region, are likely to stabilize MECIs. To examine this hypothesis, four novel pyrene derivatives, which contain highly twisted N,N-dimethylamino groups at the 4- (4-Py), 4,5- (4,5-Py), 1- (1-Py), or 1,6-positions (1,6-Py) were tested. The nonradiative transitions of 4,5-Py are highly efficient (kₙᵣ = 57.1 × 10⁷ s–¹), so that its fluorescence quantum yield in acetonitrile decreases to Φfₗ = 0.04. The solid-state fluorescence of 4,5-Py is efficient (Φfₗ = 0.49). In contrast, 1,6-Py features strong fluorescence (Φfₗ = 0.48) with a slow nonradiative transition (kₙᵣ = 11.0 × 10⁷ s–¹) that is subject to severe quenching (Φfₗ = 0.03) in the solid state. These results underline that the chemistry of the pyrene K-region is intriguing, both from a photophysical perspective and with respect to materials science.
Author Igawa, Kazunobu
Sasaki, Shunsuke
Konishi, Gen-ichi
Morokuma, Keiji
Suzuki, Satoshi
AuthorAffiliation Kyoto University
Fukui Institute for Fundamental Chemistry
Tokyo Institute of Technology
Institute for Materials Chemistry and Engineering and Department of Molecular and Material Sciences
Kyushu University
Department of Organic and Polymeric Materials
AuthorAffiliation_xml – name: Department of Organic and Polymeric Materials
– name: Kyoto University
– name: Fukui Institute for Fundamental Chemistry
– name: Kyushu University
– name: Institute for Materials Chemistry and Engineering and Department of Molecular and Material Sciences
– name: Tokyo Institute of Technology
Author_xml – sequence: 1
  givenname: Shunsuke
  surname: Sasaki
  fullname: Sasaki, Shunsuke
  email: shun.sasaki213@gmail.com
  organization: Tokyo Institute of Technology
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  givenname: Satoshi
  surname: Suzuki
  fullname: Suzuki, Satoshi
  organization: Kyoto University
– sequence: 3
  givenname: Kazunobu
  surname: Igawa
  fullname: Igawa, Kazunobu
  organization: Kyushu University
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  givenname: Keiji
  surname: Morokuma
  fullname: Morokuma, Keiji
  organization: Kyoto University
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  givenname: Gen-ichi
  orcidid: 0000-0002-6322-0364
  surname: Konishi
  fullname: Konishi, Gen-ichi
  email: konishi.g.aa@m.titech.ac.jp
  organization: Tokyo Institute of Technology
BackLink https://www.ncbi.nlm.nih.gov/pubmed/28656764$$D View this record in MEDLINE/PubMed
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Snippet A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly...
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SubjectTerms acetonitrile
anthracenes
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
energy
fluorescence
materials science
naphthalene
organic chemistry
Physical Sciences
Science & Technology
Title The K‑Region in Pyrenes as a Key Position to Activate Aggregation-Induced Emission: Effects of Introducing Highly Twisted N,N‑Dimethylamines
URI http://dx.doi.org/10.1021/acs.joc.7b00996
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https://www.ncbi.nlm.nih.gov/pubmed/28656764
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